One, remember to look up at the stars and not down at your feet. Two, never give up work. Work gives you meaning and purpose and life is empty without it. Three, if you are lucky enough to find love, remember it is there and don't throw it away.

It's been years, so I can’t remember the name of the young indian woman. But my next door neighbor was a bubbly, extroverted redhead from the midwest who worked in public relations and—apparently in a moment of sympathy—made it her mission to present me to “a few smart, cute single women in New York” in the hope that I'd find “the one”(her words, not mine). I went along with the idea and one evening found myself in a room of mostly other indian people(this could not have been coincidental), talking to an indian woman who might be a good match for me.

Our conversation was comfortable, we talked about things we like doing in the city, and found we had common friends. There was discussion of favorite restaurants in the area, and a perfunctory criticism of the indian restaurants that don't get it quite right. That was when she awkwardly veered into the topic of career—and into her non-trivial obsession with “the next 10 to 20 years.” How would she fit motherhood into life as a medical professional? Would she probably pay off her student debt in time to start racking up debt for the three kids she'd hypothetically parent with Mr. Right? My life flashed forward to two decades of living with a woman who was already always in the future. I was already feeling left behind.

She would be finishing up at Columbia University with a medical degree, and was thinking Harvard next. I already found myself listening to her less as a potential date, now she became more of a case study for people who will tolerate postponing their life for about two decades and won't realize it until they're in the latter stage of that period. The regret doesn't happen to everyone but there was one detail which made it considerably more probable with her: she was already very open about not being interested in medicine at all. “This degree and the medical career is just something that I'm doing honestly to just make my family happy.” It could have been her Bacardi and coke talking when she went on “honestly” about how much she was interested in a lot of other things like travel, which she could do but hadn't yet done. It looked like she might have to postpone that for the foreseeable future.

I needed a drink.

But as we continued it was interesting how, when discussing my career, the grass was apparently greener on my side. To her it was obvious that I had more satisfaction in my life because I was in a “creative profession.” According to her, this had little to do with me: it was my field of work that determined my satisfaction.

By then I really needed that drink.

While a certain path may be for someone and another may not, isn't it dangerous to consider any direction, in career or otherwise, as intrinsically limiting, or intrinsically free? But the perception comes up in conversations, often with people who feel trapped in their role and a lifestyle that comes with the role. They can't just walk away, the trappings are too comfortable to ignore and they secretly wish for a sign or major event to pivot their life's trajectory in a different direction. Until that moment arrives, however, it's difficult to watch someone try and embrace a journey that they have already decided is not for them.

The alternative to staying on that path isn't much better, either: often it's full of the platitude that packs the Self-Help genre.

“Be yourself! ” we tell them loudly.

“Let go of your fear! Just be you! You do you!”

"Follow your dreams!”

If it were that straightforward—if it was just about letting go of a “fear”—would we have so many intelligent, otherwise courageous people making the decision to stay put in what they know well? Should we have expected them to go in the direction of their childhood dreams?

“They just can't let go of their need for security,” is another claim from spectators.

Really? How did the simplicity of “be yourself” escape otherwise intelligent people so easily?

The problem is often more compounded and complicated than we realize. It is more than just the simple fear of taking the “road less traveled.” Because by the time you’ve made the decision to drop everything else and just be yourself, you have to stop and untangle a few other things. Since, for instance, you have no idea what that unexplored “self” is about, you have to define or—more accurately—invent your identity, decide who you are. And in order to do that, you have to first take your current self apart, and conduct an audit of your life.

Those first attempts at breaking down the old life will produce a bucket of ideas and preferences you've picked up from parents, friends, career counselors, well-wishers and authority figures. The ideas will have come with rules, regulations, etiquette and patterns of how things work, and what your participation ought to look like. To become your new self—or a self worth keeping for the long term ahead—you'd have to set new standards: learn your own rules by unlearning someone else’s.

The impulse for many, at this juncture, is to immediately search for ways to become more efficient, to not waste any more time—to do something, now because they realize that time is the precious commodity, the only real scarcity. But that kind of velocity might not be the best idea: slowing down to recalibrate is more likely to offer different possibilities, a better likelihood to not repeat the same mistakes. It’s important to realize that:

1. It is worth taking the time to figure out what you want for your Life.2. Career is secondary to what you want for your Life.

How to live your life is something you can't iterate your way into with a worksheet or list of efficiencies. Living your life shouldn't be a violent “learn to fail faster” experiment about trial and error until you get to “something that works.” No, that kind of thinking and habit is well and good for creative work, brainstorming sessions and hothouse start-up environments. But you can’t rely on that for the heavyweight foundational things that really matter in life, such as deciding who you are, or finding the right spouse, both of which deeply affect a sense of purpose and what you contribute to the world.

There are, however, a few useful concepts to designing a life around your values, with one caveat: any method of living has to be a work in progress, open to editing and coming back to, as necessary.

First, patience is something to habitually cultivate whenever you can. Because every new idea, perspective or method you introduce into your life is an investment, like furniture: you have to live with it for a while before you can decide whether it “works” for you, whether it makes you more or less balanced in how you live, and whether it sits well with everything else you already have in the room that is your heart. That kind of process—living with new things and adjusting accordingly—that takes time.

Second, resist the impulse to dismiss things that are unpleasant, only because they’re unpleasant now. The trick is to see how the uncomfortable stuff is actually the material worth studying. Appreciate the difficult side of life, and to inoculate yourself to it. Suffering—and the regular meditation on it—builds character, it gives you more fuel, more stamina for another day. For life's long run, it helps to develop lung capacity: that alone will make the difference between staring at the ground constant exhaustion while trudging forward, or having enough gas in the tank to keep your head up and fully appreciate the world as it passes by as you confidently make it to the finish line. The right journey makes the right perspective.

Third, understand that your job is to figure out how to squeeze the juice out of everything that happened to you, so that you can apply it somehow to where you are now. We spend so much of our life anxiously trimming the branch, when it might be a better idea to pay attention to the abundance of what we've cut off lying on the ground—that's where the nutrition for tomorrow sits quietly. Instead of dismissing experiences as failures, or lamenting that stars refused to line up for you when you did try, it's now your responsibility to make better sense of these things, to connect the dots from one experience to another. It's up to you to make sure to use whatever pattern you find toward a more cohesive bigger picture.

I often realize I am in the process of cultivating my own life's style. On some days it feels normal to wake up wondering whether I didn't know better then, or whether I should know better now. What is certain however is that I have no regret because it's always in my power to recalibrate and refine things as I go.